3-methylene-4-(3-nitrobenzyl)-1-(p-toluenesulfonyl)pyrrolidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-methylene-4-(3-nitrobenzyl)-1-(p-toluenesulfonyl)pyrrolidine
• 英文别名: 3-Methylidene-1-(4-methylphenyl)sulfonyl-4-[(3-nitrophenyl)methyl]pyrrolidine
• 化学式: C₁₉H₂₀N₂O₄S
• 分子量: 372.445
• InChiKey: AEMAOMADGJXWMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-烯丙基对甲苯磺酰胺 在 四(三苯基膦)钯 sodium carbonate 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 12.0h， 生成 3-methylene-4-(3-nitrobenzyl)-1-(p-toluenesulfonyl)pyrrolidine
  参考文献：
  名称：

  Suppressed β-Hydride Elimination in Palladium-Catalyzed Cascade Cyclization−Coupling Reactions:  An Efficient Synthesis of 3-Arylmethylpyrrolidines

  摘要：

  A novel type of palladium-catalyzed cascade cyclization-coupling reaction that proceeds with suppressed beta-hydride elimination has been found. One of the N-sulfonyl oxygens is suggested to coordinatively stabilize an alkylpalladium intermediate, thus preventing the intermediate from the usual beta-elimination, This is the first sequential palladium-catalyzed coupling reaction where the Suzuki and Heck reactions can compete. The reaction provides an efficient synthetic route to 4-methylene-3-arylmethylpyrrolidines, which are not readily available by other routes.

  DOI：

  10.1021/ol0056426

文献信息

• Suppressed β-Hydride Elimination in Palladium-Catalyzed Cascade Cyclization−Coupling Reactions:  An Efficient Synthesis of 3-Arylmethylpyrrolidines
  作者：Chi-Wan Lee、Kyung Seok Oh、Kwang S. Kim、Kyo Han Ahn

  DOI：10.1021/ol0056426

  日期：2000.5.1

  A novel type of palladium-catalyzed cascade cyclization-coupling reaction that proceeds with suppressed beta-hydride elimination has been found. One of the N-sulfonyl oxygens is suggested to coordinatively stabilize an alkylpalladium intermediate, thus preventing the intermediate from the usual beta-elimination, This is the first sequential palladium-catalyzed coupling reaction where the Suzuki and Heck reactions can compete. The reaction provides an efficient synthetic route to 4-methylene-3-arylmethylpyrrolidines, which are not readily available by other routes.